The ability to pay checks in QBO has been nearly eliminated to make it easier for Intuit to profit off our paying bills. As stated in previous employees statements here the investigation is closed and it's not going to change. The only work around I've found, is to do screenshots of the Expenses > Vendor detail to get my bill date and then go to bill pay and manually reconcile the screenshot to the bills that need to be paid.

Paying bills to print checks is no longer a practical function of QBO if your vendor has due dates on a specific day in the following month. Items like 30 day from bill due dates work fine but items purchased in April and due the 10th of May is very difficult to pay the oldest invoices first.

I will thank the Intuit team for finally pushing me to realize I need to take the time to find better software.